Monoazo dyestuffs soluble in water



Patented Oct. 10, 1939 UNITED STATES PATENT OFFICE MONOAZO DYESTUFFSSOLUBLE IN WATER Erich Fischer and Walter Gmelin, Bad Soden in Taunus,Germany, assignors to General Aniline Works, Inc., New York, N. Y., acorporation of Delaware No Drawing. Application March 19, 1938, SerialNo. 196,901. In Germany March 24, 1937 5 Claims.

wherein R. stands for an aryl radical not containing any group lendingsolubility and X stands for hydrogen or alkyl.

We have found that valuable monoazo-dyestuffs soluble in water areobtainable by combining in an acid or alkaline medium with anydiazo-compound of the benzene series not containing any group lendingsolubility, an aminohydroxynaphthalene of the general constitution:

wherein R stands for a naphthalene nucleus which may contain furthersubstituents, but must not contain a sulfonic acid group, X stands forhydrogen or alkyl with the proviso that derivatives of1-amino-7-hydroxynaphthalene are excluded.

The dyestuffs thus obtained are especially suitable for dyeing woolyellow-brown, brown-red to Bordeaux-red tints from an acid bath belowboiling temperature, for instance, at 60 to 90 C.

The sulfoalkylamino-hydroxynaphthalenes used as coupling components maybe obtained by condensing the corresponding amino-hydroxynaphthaleneswith halogenalkylsulfonic acids.

The following examples serve to illustrate the invention, but they arenot intended to limit it thereto, the parts being by weight, unlessotherwise stated. The ratio between parts by weight and parts by volumeis that which exists between the kilo and the liter:

1. Into a solution obtained from 253 parts of2-sulfethylamino-7-hydroxynaphthalene, water and 212 parts of sodiumcarbonate there is run a diazo-solution prepared in the usual mannerfrom 93 parts of aminobenzene. When the coupling is complete thedyestuff is salted out, fil tered with suction and dried. It dyes woolthroughout in an acid bath below boiling temperature, for instance at 60C. to 80 (3., redbrown even tints. The dyestuff corresponds with thefollowing formula:

2. If in Example 1 the aminobenzene is exchanged for 107 parts of1-amino-2-methylbenzene, a dyestuif of similar properties is obtained.

3. By combining a diazo-solution from 151 parts of 1-aminobenz ene-3-carboxylic jacid methyl-ester with a solution of 253 parts of 2-sulfethylamino-Z-hydroxynaphthalene or 267 parts of2-sulfop-ropylamino-'7-hydroxynaphthalene and 220 parts of sodiumcarbonate in water there are obtained after salting out dyestufis whichdye wool throughout already at 70 C. from an acid bath full brown eventints.

4. If in Example 3 the l-aminobenzene-3-carboxylic acid methyl-ester isexchanged for 147 parts of 1-amino-5.6.7.8-tetrahydronaphthalene, ared-brown product is obtained which dyes wool throughout below boilingtemperature from an acid bath Bordeaux even tints.

5. If in Example 1 the 2-sulfethylamino-7-hydroxynaphthalene isexchanged for 253 parts of 2-.sulfethylamino-fi-hydroxynaphthalene adyestuff of similar properties is obtained.

6. A dyestuif dyeing wool below boiling temperature in an acid bathbrown-red even tints is obtained if in Example 1 the 2-sulfethylamino-7-hydroxynaphthalene is exchanged for the same Weight of2-sulfethylamino-8-hydroxynaphthalene.

7. 107 parts of l-amino-i-methoxybenzene are diazotised in the usualmanner and the diazosolution is combined in the presence of sodiumcarbonate in excess with an aqueous solution of 239 parts of2-sulfomethylamino-'I-hydroxynaphthalene, while cooling. The dyestuffobtained is salted out and dried. It dyes wool throughout at 60 to 80 C.in an acid bath brownred tints.

8. 127.5 parts of 1-amino-3-chl0robenzene are diazotised in the usualmanner and the diazocompound is introduced into a well cooled solutionof 267 parts of 2-sulfethylmethylamino-7- hydroxynaphthalene renderedalkaline by means of sodium carbonate. When the coupling is complete theproduct obtained is salted out, filtered with suction and dried. Adyestuff is obtained which dyes wool throughout below boilingtemperature in an acid bath red even tints.

9. If in Example 8 the Z-sulfethylmethylamino-l-hydroxynaphthalene isexchanged for 281 parts of 2-sulfethyl-ethylamino-7-hydroxynaphthalene adyestufi" of similar properties is obtained.

10. 123 parts of l-amino-i-methoxybenzene are diazotised in hydrochloricacid in excess with 69 parts of sodium nitrite. The diazo-solutionobtained is run into an aqueous solution, cooled to C., of 253 parts of2-sulfethylamino-7-hydroxynaphthalene and sodium. carbonate in excess.The dyestufi? obtained is separated by means of sodium chloride anddried. It is a brown powder which dissolves easily in water and has theproperty of dying W001 throughout in an acid bath, for instance, at 70C. Bordeaux-brown even tints.

We claim:

1. The water-soluble monoazo-dyestufis of the following general formula:

wherein R means a radical of the benzene series not containing a grouplending solubility, X stands for one of the group consisting of hydrogenmethyl and ethyl, and Y for one of the group consisting of methyl, ethyland propyl, being brown powders which dye wool from an acid bath belowboiling temperature, at 60 C. to 90 C., yellow-brown, brown-red toBordeaux-red even shades.

2. The water-soluble monoazo-dyestufis of the following general formula:

HO N wherein R means a radical of the benzene series not containing agroup lending solubility, X stands for one of the group consisting ofhydrobeing a brown powder which dyes wool throughout in an acid bathbelow boiling temperature, for instance at 60 C.-80 C., red-brown evenshades.

4. The water-soluble monoazo-dyestufi of the following formula:

being a brown powder which dyes wool throughout in an acid bath belowboiling temperature, for instance, at 70 C., full brown even shades.

5. The water-soluble monoazo-dyestuff of the following formula:

being a brown powder which dissolves easily in water and dyes woolthroughout in an acid bath below boiling temperature, for instance, at70 C., Bordeaux-brown even shades.

ERICH FISCHER. WALTER GMELJN.

